Aluminum Chloride Promoted Cross-Coupling of Trisubstituted Enol Phosphates with Organozinc Reagents En Route to the Stereoselective Synthesis of Tamoxifen and Its Analogues

被引：21

作者：

Kotek, Vladislav ^{[1
]}

Polak, Peter ^{[1
]}

Dvorakova, Hana ^{[2
]}

Tobrman, Tomas ^{[1
]}

机构：

[1] Univ Chem & Technol, Dept Organ Chem, Tech 5, Prague 16628 6, Czech Republic

[2] Univ Chem & Technol, Lab NMR Spect, Tech 5, Prague 16628 6, Czech Republic

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 29期

关键词：

Alkenes; Cross-coupling; Lewis acids; C-C coupling; Synthetic methods; CARBON TETRASUBSTITUTED ALKENES; SUBSTITUTED ALPHA; BETA-UNSATURATED ESTERS; PHOSPHOENOL RADICAL CATIONS; ONE-ELECTRON OXIDATION; O BOND-CLEAVAGE; STEREOSPECIFIC SYNTHESIS; GRIGNARD-REAGENTS; DOMINO REACTIONS; MCMURRY REACTION; OLEFINS;

D O I：

10.1002/ejoc.201600959

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the stereoselective cross-coupling reaction of arylzinc chlorides with trisubstituted enol phosphates is described. The developed method requires aluminum chloride as a promoter, and the reaction conditions tolerate various functional groups. The observed reactivity pattern of trisubstituted enol phosphates was used for the stereoselective preparation of tamoxifen and its analogues.

引用

页码：5037 / 5044

页数：8

共 10 条

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